UA58505C2 - 2-аміно-4-біциклоаміно-1,3,5-триазини, гербіцидний засіб або засіб для регулювання росту рослин та спосіб боротьби з шкідливими рослинами або регулювання росту рослин - Google Patents
2-аміно-4-біциклоаміно-1,3,5-триазини, гербіцидний засіб або засіб для регулювання росту рослин та спосіб боротьби з шкідливими рослинами або регулювання росту рослин Download PDFInfo
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- UA58505C2 UA58505C2 UA98095076A UA98095076A UA58505C2 UA 58505 C2 UA58505 C2 UA 58505C2 UA 98095076 A UA98095076 A UA 98095076A UA 98095076 A UA98095076 A UA 98095076A UA 58505 C2 UA58505 C2 UA 58505C2
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- Ukraine
- Prior art keywords
- alkyl
- residues
- group
- residue
- cyclic
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- 238000000034 method Methods 0.000 title claims abstract description 20
- 239000004009 herbicide Substances 0.000 title claims abstract description 11
- 239000005648 plant growth regulator Substances 0.000 title claims abstract description 8
- 230000002363 herbicidal effect Effects 0.000 title claims description 12
- 230000008635 plant growth Effects 0.000 title claims description 4
- 241000196324 Embryophyta Species 0.000 title description 41
- 230000033228 biological regulation Effects 0.000 title description 2
- 230000001629 suppression Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 150000003839 salts Chemical class 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims description 428
- -1 cyano, thiocyanato Chemical group 0.000 claims description 117
- 125000000623 heterocyclic group Chemical group 0.000 claims description 85
- 125000005843 halogen group Chemical group 0.000 claims description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 125000004122 cyclic group Chemical group 0.000 claims description 65
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 125000003342 alkenyl group Chemical group 0.000 claims description 63
- 150000002367 halogens Chemical class 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 55
- 125000005842 heteroatom Chemical group 0.000 claims description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims description 52
- 239000001257 hydrogen Substances 0.000 claims description 51
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 50
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 49
- 125000003282 alkyl amino group Chemical group 0.000 claims description 47
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 47
- 125000004414 alkyl thio group Chemical group 0.000 claims description 46
- 125000001188 haloalkyl group Chemical group 0.000 claims description 45
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 41
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 26
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 24
- 125000002015 acyclic group Chemical group 0.000 claims description 23
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 22
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 20
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 16
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 15
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 14
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 8
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000004442 acylamino group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 125000004440 haloalkylsulfinyl group Chemical group 0.000 claims description 5
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 5
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 230000001105 regulatory effect Effects 0.000 claims description 3
- 125000000232 haloalkynyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims 1
- 229940067606 lecithin Drugs 0.000 claims 1
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- 239000000787 lecithin Substances 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 125000000858 thiocyanato group Chemical group *SC#N 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 abstract description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 39
- 239000010949 copper Substances 0.000 description 32
- 239000013543 active substance Substances 0.000 description 31
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- 239000002253 acid Substances 0.000 description 26
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 19
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 150000002148 esters Chemical class 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 238000009835 boiling Methods 0.000 description 13
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- 238000006243 chemical reaction Methods 0.000 description 13
- 150000004678 hydrides Chemical class 0.000 description 13
- 150000004679 hydroxides Chemical class 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
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- 239000000243 solution Substances 0.000 description 11
- 238000005507 spraying Methods 0.000 description 11
- 150000001342 alkaline earth metals Chemical class 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- 229910052783 alkali metal Inorganic materials 0.000 description 9
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- 125000003118 aryl group Chemical group 0.000 description 9
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- 125000001424 substituent group Chemical group 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- 125000006530 (C4-C6) alkyl group Chemical group 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
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- 235000011152 sodium sulphate Nutrition 0.000 description 6
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- 150000001298 alcohols Chemical class 0.000 description 4
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 238000007796 conventional method Methods 0.000 description 3
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 3
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- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 2
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- ABOOPXYCKNFDNJ-SNVBAGLBSA-N quizalofop-P Chemical compound C1=CC(O[C@H](C)C(O)=O)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 ABOOPXYCKNFDNJ-SNVBAGLBSA-N 0.000 description 1
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
- 235000002079 ragi Nutrition 0.000 description 1
- 235000020079 raki Nutrition 0.000 description 1
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000008259 solid foam Substances 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- PQTBTIFWAXVEPB-UHFFFAOYSA-N sulcotrione Chemical compound ClC1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O PQTBTIFWAXVEPB-UHFFFAOYSA-N 0.000 description 1
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- ZDXMLEQEMNLCQG-UHFFFAOYSA-N sulfometuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ZDXMLEQEMNLCQG-UHFFFAOYSA-N 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- BCQMBFHBDZVHKU-UHFFFAOYSA-N terbumeton Chemical compound CCNC1=NC(NC(C)(C)C)=NC(OC)=N1 BCQMBFHBDZVHKU-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
- 229960003231 thioacetazone Drugs 0.000 description 1
- 150000003566 thiocarboxylic acids Chemical class 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19607450A DE19607450A1 (de) | 1996-02-28 | 1996-02-28 | 2-Amino-4-bicycloamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
PCT/EP1997/000702 WO1997031904A1 (de) | 1996-02-28 | 1997-02-14 | 2-amino-4-bicycloamino-1,3,5-triazine als herbizide und pflanzenwachstumsregulatoren |
Publications (1)
Publication Number | Publication Date |
---|---|
UA58505C2 true UA58505C2 (uk) | 2003-08-15 |
Family
ID=7786633
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA98095076A UA58505C2 (uk) | 1996-02-28 | 1997-02-14 | 2-аміно-4-біциклоаміно-1,3,5-триазини, гербіцидний засіб або засіб для регулювання росту рослин та спосіб боротьби з шкідливими рослинами або регулювання росту рослин |
Country Status (23)
Country | Link |
---|---|
US (1) | US6069114A (de) |
EP (1) | EP0885201A1 (de) |
JP (1) | JP4442931B2 (de) |
KR (1) | KR100849899B1 (de) |
CN (1) | CN1083439C (de) |
AU (1) | AU714187B2 (de) |
BG (1) | BG64096B1 (de) |
BR (1) | BR9707781B1 (de) |
CA (1) | CA2248338C (de) |
CL (1) | CL2004001102A1 (de) |
CZ (1) | CZ296253B6 (de) |
DE (1) | DE19607450A1 (de) |
HU (1) | HUP9901113A3 (de) |
ID (1) | ID16056A (de) |
MX (1) | MX9807064A (de) |
MY (1) | MY118281A (de) |
PL (1) | PL195265B1 (de) |
RU (1) | RU2314297C2 (de) |
TR (1) | TR199801714T2 (de) |
TW (1) | TW368395B (de) |
UA (1) | UA58505C2 (de) |
WO (1) | WO1997031904A1 (de) |
ZA (1) | ZA971642B (de) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR19990071656A (ko) * | 1995-11-27 | 1999-09-27 | 도미나가 가즈토 | 트리아진 유도체 |
DE19830902A1 (de) | 1998-07-10 | 2000-01-13 | Hoechst Schering Agrevo Gmbh | Verfahren zur Herstellung von 2-Amino-4-chlor-1,3,5-triazinen |
DE19842894A1 (de) * | 1998-09-18 | 2000-03-23 | Hoechst Schering Agrevo Gmbh | Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen |
DE19921883A1 (de) * | 1999-05-12 | 2000-11-16 | Bayer Ag | Substituierte Thienocycloalk(en)ylamino-1,3,5-triazine |
JP2001151612A (ja) * | 1999-09-09 | 2001-06-05 | Nippon Bayer Agrochem Co Ltd | 除草性1,3,5−トリアジン類 |
GB0026010D0 (en) * | 2000-10-24 | 2000-12-13 | Air Prod & Chem | N-fluorotriazinium fluorinating agents |
GB0026012D0 (en) | 2000-10-24 | 2000-12-13 | Air Prod & Chem | Electrophilic fluorination |
EP2206703A1 (de) * | 2008-12-30 | 2010-07-14 | Bayer CropScience AG | Pyrimidinderivate und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums |
DE10207037A1 (de) | 2002-02-20 | 2003-08-28 | Bayer Cropscience Gmbh | 2-Amino-4-bicyclyamino-6H-1,3.5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
MXPA05008295A (es) * | 2003-02-05 | 2005-09-20 | Bayer Cropscience Gmbh | Amino-1,3,5-triazinas sustituidas en n con radicales biciclicos quirales, procedimiento para su preparacion, composiciones de las mismas, y su uso como herbicidas y reguladores del crecimiento de las plantas. |
DE102004034571A1 (de) * | 2004-07-17 | 2006-02-23 | Bayer Cropscience Gmbh | Herbizide Mittel |
EP1836894A1 (de) | 2006-03-25 | 2007-09-26 | Bayer CropScience GmbH | Neue Sulfonamid-haltige feste Formulungen |
EP1790227A1 (de) | 2005-11-25 | 2007-05-30 | Bayer CropScience AG | Wässrige Suspensionskonzentrate aus 2,4-Diamino-s-triazinherbiziden |
EP1854355A1 (de) * | 2006-03-15 | 2007-11-14 | Bayer CropScience AG | Wässrige Suspensionskonzentrate |
EP1844654A1 (de) | 2006-03-29 | 2007-10-17 | Bayer CropScience GmbH | Penetrationsförderer für agrochemische Wirkstoffe |
DE102007013362A1 (de) | 2007-03-16 | 2008-09-18 | Bayer Cropscience Ag | Penetrationsförderer für herbizide Wirkstoffe |
DE102006016885A1 (de) * | 2006-04-11 | 2007-10-18 | Bayer Cropscience Ag | Mit bicyclischen Radikalen N-substituierte Diamino-1,3,5-triazine, Verfahren für ihre Herstellung, Zubereitungen davon und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE102006016884A1 (de) * | 2006-04-11 | 2007-10-25 | Bayer Cropscience Ag | Substituierte Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
DE102006059941A1 (de) | 2006-12-19 | 2008-06-26 | Bayer Cropscience Ag | Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
EP1958509A1 (de) * | 2007-02-19 | 2008-08-20 | Bayer CropScience AG | Herbizid-Kombination |
EP2092825A1 (de) | 2008-02-21 | 2009-08-26 | Bayer CropScience Aktiengesellschaft | Herbizid-Kombinationen enthaltend ein Herbizid der Klasse der Diamino-s-triazine |
EP2147600A1 (de) * | 2008-07-21 | 2010-01-27 | Bayer CropScience AG | Verfahren zur Kontrolle von Unkraut in Rasen |
EP2210879A1 (de) * | 2008-12-30 | 2010-07-28 | Bayer CropScience AG | Pyrimidinderivate und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwachstums |
WO2011076731A1 (de) | 2009-12-23 | 2011-06-30 | Bayer Cropscience Ag | Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid |
CN103281905B (zh) | 2010-12-21 | 2016-10-19 | 拜尔作物科学有限合伙公司 | 芽孢杆菌属的砂纸突变体及其用于增进植物生长、促进植物健康及控制疾病和害虫的方法 |
EP2755485A1 (de) | 2011-09-12 | 2014-07-23 | Bayer Cropscience LP | Verfahren zur verbesserung der gesundheit und/oder der förderung des wachstums einer pflanze und/oder zur verbesserung der fruchtreifung |
US10479777B2 (en) * | 2013-07-16 | 2019-11-19 | Basf Se | Herbicidal azines |
EP2930174A1 (de) * | 2014-04-07 | 2015-10-14 | Basf Se | Diaminotriazinderivate als Herbizide |
WO2015155129A1 (en) * | 2014-04-07 | 2015-10-15 | Basf Se | Diaminotriazine compound |
AU2015250900B9 (en) | 2014-04-23 | 2019-03-21 | Basf Se | Diaminotriazine compounds as herbicides |
KR101630161B1 (ko) * | 2014-07-25 | 2016-06-14 | 한국화학연구원 | 열안정성이 우수한 탄성 폴리우레탄의 중합 방법 및 이로부터 제조된 탄성 폴리우레탄 중합체 |
WO2016079035A1 (en) | 2014-11-18 | 2016-05-26 | Bayer Cropscience Aktiengesellschaft | Use of certain herbicide combinations in tuberous root crop plants |
EP3288381A1 (de) | 2015-04-27 | 2018-03-07 | Bayer CropScience Aktiengesellschaft | Herbizidkombinationen mit glufosinaten und indaziflam |
KR102632658B1 (ko) | 2015-05-11 | 2024-02-01 | 바스프 에스이 | L-글루포시네이트 및 인다지플람을 포함하는 제초제 조합물 |
CA3046044A1 (en) | 2016-12-07 | 2018-06-14 | Bayer Cropscience Aktiengesellschaft | Herbicidal combination containing triafamone and indaziflam |
CN110461833A (zh) * | 2017-04-05 | 2019-11-15 | 拜耳作物科学股份公司 | 2-氨基-5-氧基烷基嘧啶衍生物及其用于防治不希望的植物生长的用途 |
BR112020011214A2 (pt) * | 2017-12-04 | 2020-11-17 | Bayer Cropscience Aktiengesellschaft | derivados de 3-amino-[1,2,4]-triazol e seu uso para controlar o crescimento indesejado de plantas. |
MX2022012658A (es) | 2020-04-09 | 2022-11-07 | Bayer Ag | Nueva combinacion de compuestos con superior actividad herbicida. |
US20230128357A1 (en) | 2020-04-09 | 2023-04-27 | Bayer Aktiengesellschaft | Compound Combination with Superior Herbicidal Activity |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3816419A (en) * | 1972-10-27 | 1974-06-11 | American Cyanamid Co | Substituted s-triazines |
US3932167A (en) * | 1972-10-27 | 1976-01-13 | American Cyanamid Company | Substituted s-triazines as herbicidal agents |
US4932998A (en) * | 1986-09-30 | 1990-06-12 | Idemitsu Kosan Company Limited | Triazine derivatives, and herbicides comprising the same as the effective ingredient |
EP0283522B1 (de) * | 1986-09-30 | 1991-02-27 | Idemitsu Kosan Company Limited | Triazinderivate, deren herstellung und unkrautvertilgungsmittel daraus |
KR940001728B1 (ko) * | 1989-02-20 | 1994-03-05 | 이데미쓰 고산 가부시끼가이샤 | 트리아진 유도체 및 그것을 유효성분으로 하는 제초제 |
US5286905A (en) * | 1990-12-28 | 1994-02-15 | Idemitsu Kosan Company Limited | Process for producing biguanide derivative |
US5250686A (en) * | 1991-04-18 | 1993-10-05 | Idemitsu Kosan Company Limited | Process for producing triazine compounds |
DE69405502T2 (de) * | 1993-04-08 | 1998-01-15 | Idemitsu Kosan Co | Verfahren zur herstellung von 2-fluor isobuttersäure und deren ester |
JPH08183781A (ja) * | 1994-12-28 | 1996-07-16 | Idemitsu Kosan Co Ltd | トリアジン誘導体およびそれを有効成分とする除草剤 |
DE19522137A1 (de) * | 1995-06-19 | 1997-01-02 | Hoechst Schering Agrevo Gmbh | 2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
-
1996
- 1996-02-28 DE DE19607450A patent/DE19607450A1/de not_active Withdrawn
-
1997
- 1997-02-14 EP EP97903284A patent/EP0885201A1/de not_active Ceased
- 1997-02-14 KR KR1019980706747A patent/KR100849899B1/ko active IP Right Grant
- 1997-02-14 HU HU9901113A patent/HUP9901113A3/hu not_active Application Discontinuation
- 1997-02-14 UA UA98095076A patent/UA58505C2/uk unknown
- 1997-02-14 CA CA002248338A patent/CA2248338C/en not_active Expired - Lifetime
- 1997-02-14 TR TR1998/01714T patent/TR199801714T2/xx unknown
- 1997-02-14 CZ CZ0276198A patent/CZ296253B6/cs not_active IP Right Cessation
- 1997-02-14 BR BRPI9707781-0A patent/BR9707781B1/pt not_active IP Right Cessation
- 1997-02-14 RU RU98117853/04A patent/RU2314297C2/ru active
- 1997-02-14 PL PL97328660A patent/PL195265B1/pl unknown
- 1997-02-14 JP JP53054497A patent/JP4442931B2/ja not_active Expired - Lifetime
- 1997-02-14 AU AU17693/97A patent/AU714187B2/en not_active Expired
- 1997-02-14 WO PCT/EP1997/000702 patent/WO1997031904A1/de not_active Application Discontinuation
- 1997-02-14 CN CN97192683A patent/CN1083439C/zh not_active Expired - Lifetime
- 1997-02-25 US US08/805,576 patent/US6069114A/en not_active Expired - Lifetime
- 1997-02-26 TW TW086102346A patent/TW368395B/zh not_active IP Right Cessation
- 1997-02-26 ZA ZA9701642A patent/ZA971642B/xx unknown
- 1997-02-26 MY MYPI97000728A patent/MY118281A/en unknown
- 1997-02-27 ID IDP970588A patent/ID16056A/id unknown
-
1998
- 1998-08-20 BG BG102706A patent/BG64096B1/bg unknown
- 1998-08-28 MX MX9807064A patent/MX9807064A/es unknown
-
2004
- 2004-05-18 CL CL200401102A patent/CL2004001102A1/es unknown
Also Published As
Publication number | Publication date |
---|---|
MX9807064A (es) | 1998-12-31 |
KR19990087338A (ko) | 1999-12-27 |
ZA971642B (en) | 1997-11-25 |
US6069114A (en) | 2000-05-30 |
CA2248338C (en) | 2008-09-02 |
TW368395B (en) | 1999-09-01 |
PL328660A1 (en) | 1999-02-15 |
CA2248338A1 (en) | 1997-09-04 |
BG102706A (en) | 1999-04-30 |
BG64096B1 (bg) | 2003-12-31 |
HUP9901113A1 (hu) | 1999-07-28 |
HUP9901113A3 (en) | 2000-06-28 |
EP0885201A1 (de) | 1998-12-23 |
RU2314297C2 (ru) | 2008-01-10 |
CN1212687A (zh) | 1999-03-31 |
TR199801714T2 (xx) | 1998-12-21 |
CL2004001102A1 (es) | 2005-04-29 |
BR9707781B1 (pt) | 2010-10-05 |
KR100849899B1 (ko) | 2010-06-15 |
JP2000505462A (ja) | 2000-05-09 |
AU714187B2 (en) | 1999-12-23 |
CZ276198A3 (cs) | 1998-12-16 |
JP4442931B2 (ja) | 2010-03-31 |
CN1083439C (zh) | 2002-04-24 |
ID16056A (id) | 1997-08-28 |
PL195265B1 (pl) | 2007-08-31 |
DE19607450A1 (de) | 1997-09-04 |
MY118281A (en) | 2004-09-30 |
CZ296253B6 (cs) | 2006-02-15 |
BR9707781A (pt) | 1999-07-27 |
WO1997031904A1 (de) | 1997-09-04 |
AU1769397A (en) | 1997-09-16 |
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